Chalcogen⋅⋅⋅π Bonding Catalysis
Xiangjin Kong, Panpan Zhou, Yao Wang
Abstract
Abstract While the presence of sulfur⋅⋅⋅π bonding interaction is a general phenomenon in the biological systems, the exploitation of this noncovalent force in a chemical process yet remains elusive. Herein, we describe the concept of chalcogen⋅⋅⋅π bonding catalysis that activates molecules of π systems through the interaction between chalcogen and π‐electron cloud. The proof‐of‐concept studies using a vinylindole‐based Diels–Alder benchmark reaction demonstrate that S⋅⋅⋅π and Se⋅⋅⋅π bonding interaction can drive the cycloaddition reaction efficiently. Experimental results suggest that a simultaneously double Se⋅⋅⋅π bonding interaction directs the stereoselectivity in this cycloaddition process.
Topics & Concepts
ChalcogenCycloadditionChemistryNon-covalent interactionsCatalysisMoleculeComputational chemistryNanotechnologyCombinatorial chemistryOrganic chemistryMaterials scienceHydrogen bondOrganic Chemistry Cycloaddition ReactionsSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis